GB830857A - Aminoalkyl aryl ethers - Google Patents
Aminoalkyl aryl ethersInfo
- Publication number
- GB830857A GB830857A GB3011/58A GB301158A GB830857A GB 830857 A GB830857 A GB 830857A GB 3011/58 A GB3011/58 A GB 3011/58A GB 301158 A GB301158 A GB 301158A GB 830857 A GB830857 A GB 830857A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- benzoate
- ethyl
- compounds
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0830857/IV (b)/1> (wherein R is methyl or ethyl, R1 is methylene, ethylene or propylene, R11 is methyl or ethyl and R111 is hydrogen, methyl or ethyl, or R11 and R111 may, together with the vicinal nitrogen atom, form a saturated heterocyclic ring) and acid-addition salts thereof; and their preparation by reacting an alkyl 2-hydroxy-3-methyl-benzoate with a reactive ester of an appropriate tertiary amino alcohol. Suitable reactive esters are halides or alkyl- or aryl-sulphonic esters and the reaction is advantageously carried out in a solvent in the presence of an acid acceptor such as an alkali metal hydroxide, alcoholate or carbonate. The compounds may also be prepared by reacting the benzoate with, for example, a phthalimidoalkyl halide, a halocarboxamide or a nitrile of a halocarboxylic acid and then converting the phthalimido, carboxamide or nitrile group into an amino group and alkylating this. Amino-propyl ethers may also be prepared by reacting the benzoate with the corresponding acrylic acid derivatives. A further method for the preparation of the compounds of the invention comprises the splitting off of carbon dioxide from the corresponding carbonates. Examples describe the preparation of compounds wherein R in the above general formula is variously methyl and ethyl, R1 is variously ethylene, trimethylene and propylene and -NR11R111 is variously dimethylamino, diethylamino, piperidino and morpholino, hydrochlorides and phosphates of some of the products also being described. In further examples, methyl 2-hydroxy-3-methyl benzoate sodium salt and p-toluene sulphonic acid b -chloroethyl ester give methyl-2-(b -dimethylamino-ethoxy)-3-methyl-benzoate and this with dimethylamine gives methyl 2-(b -dimethylamino-ethoxy)-3-methyl-benzoate, which is also prepared by the action of dimethylamine on methyl 2-(b -bromo-ethoxy)-3-methyl-benzoate, itself prepared from the sodium salt of methyl 2-hydroxy-3-methyl-benzoate and ethylene dibromide. Specification 822,931 is referred to.ALSO:Veterinary and pharmaceutical anaesthetic compositions comprise one or more compounds of the formula <FORM:0830857/VI/1> (wherein R is methyl or ethyl, R1 is methylene, ethylene or propylene, R11 is methyl or ethyl and R111 is hydrogen, methyl or ethyl, or R11 and R111 may, together with the vicinal nitrogen atom, form a saturated heterocyclic ring) or acid-addition salts thereof in admixture with a pharmaceutical carrier or carriers. Specification 822,931 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF22404A DE1118219B (en) | 1957-02-21 | 1957-02-21 | Process for the preparation of basic substituted alkyl ethers of o-cresotinic acid esters and their salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB830857A true GB830857A (en) | 1960-03-23 |
Family
ID=7090428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3011/58A Expired GB830857A (en) | 1957-02-21 | 1958-01-29 | Aminoalkyl aryl ethers |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT203001B (en) |
| DE (1) | DE1118219B (en) |
| DK (2) | DK89717C (en) |
| FR (1) | FR1241124A (en) |
| GB (1) | GB830857A (en) |
| NL (1) | NL225119A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1288066A (en) * | 1968-09-16 | 1972-09-06 | ||
| FR2192811B1 (en) * | 1972-07-20 | 1975-08-08 | Centre Etd Ind Pharma | |
| FR2215217A1 (en) * | 1973-01-23 | 1974-08-23 | Centre Etd Ind Pharma | Ortho thymotic acid di alkyl amines - coronary dilators, anti arrhythmic agents, local anaesthetics and antitussives |
| IT1051445B (en) * | 1975-07-16 | 1981-04-21 | Recordati Chem Pharm | THERAPEUTICALLY ACTIVE BENZOIC ACID DERIVATIVES AND PROCEDURE TO PREPARE THEM |
-
1957
- 1957-02-21 DE DEF22404A patent/DE1118219B/en active Pending
-
1958
- 1958-01-22 AT AT46558A patent/AT203001B/en active
- 1958-01-29 GB GB3011/58A patent/GB830857A/en not_active Expired
- 1958-02-19 FR FR758584A patent/FR1241124A/en not_active Expired
- 1958-02-20 NL NL225119A patent/NL225119A/xx unknown
- 1958-02-20 DK DK60358A patent/DK89717C/en active
- 1958-02-20 DK DK403958A patent/DK93084C/en active
Also Published As
| Publication number | Publication date |
|---|---|
| NL225119A (en) | 1962-10-15 |
| DK93084C (en) | 1962-03-26 |
| AT203001B (en) | 1959-04-25 |
| DE1118219B (en) | 1961-11-30 |
| DK89717C (en) | 1960-09-19 |
| FR1241124A (en) | 1960-09-16 |
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